(3-Chlorophenyl)boronic acid → HCID 90036024, compound

HRID 925808Notes

Reaction equation

HRID 925808 reaction equation
Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]3=[CH:7][C:6]=2[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1>>[Cl:18][C:19]1[CH:24]=[C:23]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[CH:7][C:6]=3[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=2)[CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 90036024HCID 90036024, compound

Procedure

The title compound, off-white solid (73 mg, 91%), MS (ISP) m/z=322.4 [(M+H)+], mp 241.5° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 15) (72.5 mg, 0.25 mmol) and commercially available 3-chloro-phenylboronic acid (50.8 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-6232018da80141df9a303fde6caa335e
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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